Human Metabolome Database: Showing metabocard for PC(P-18:1(11Z)/P-18:1(11Z)) (HMDB0011300)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (44) Show 44 proteins XML

enzymes (44) Show 44 proteins

Record Information

Version

4.0

Status

Detected and Quantified

Creation Date

2008-12-10 02:07:10 UTC

Update Date

2020-02-26 21:34:51 UTC

HMDB ID

HMDB0011300

Secondary Accession Numbers

HMDB11300

Metabolite Identification

Common Name

PC(P-18:1(11Z)/P-18:1(11Z))

Description

PC(P-18:1(11Z)/P-18:1(11Z)) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(P-18:1(11Z)/P-18:1(11Z)), in particular, consists of two chains of plasmalogen 18:1n7 at the C-1 and C-2 positions. The plasmalogen 18:1n7 moieties are derived from animal fats, liver and kidney. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2R)-2,3-Bis[(1Z,11Z)-octadeca-1,11-dien-1-yloxy]propyl 2-(trimethylazaniumyl)ethyl phosphoric acid	Generator, HMDB

Chemical Formula

C₄₄H₈₄NO₆P

Average Molecular Weight

754.131

Monoisotopic Molecular Weight

753.603626427

IUPAC Name

(2R)-2,3-bis[(1Z,11Z)-octadeca-1,11-dien-1-yloxy]propyl 2-(trimethylazaniumyl)ethyl phosphate

Traditional Name

(2R)-2,3-bis[(1Z,11Z)-octadeca-1,11-dien-1-yloxy]propyl 2-(trimethylammonio)ethyl phosphate

CAS Registry Number

Not Available

SMILES

[H][C@@](CO\C=C/CCCCCCCC\C=C/CCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)O\C=C/CCCCCCCC\C=C/CCCCCC

InChI Identifier

InChI=1S/C44H84NO6P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-39-48-42-44(43-51-52(46,47)50-41-38-45(3,4)5)49-40-37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h16-19,36-37,39-40,44H,6-15,20-35,38,41-43H2,1-5H3/b18-16-,19-17-,39-36-,40-37-/t44-/m1/s1

InChI Key

LTQBTADUGKSCOZ-WRCNLVTNSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as glycerophosphocholines. These are lipids containing a glycerol moiety carrying a phosphocholine at the 3-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphocholines

Direct Parent

Glycerophosphocholines

Alternative Parents

Substituents

Glycero-3-phosphocholine
Phosphocholine
Glycerol vinyl ether
Dialkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Quaternary ammonium salt
Tetraalkylammonium salt
Amine
Organic salt
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Source:

Biological location:

Tissue and substructures:

All tissues

Biofluid and excreta:

Cell and elements:

Extracellular

Subcellular:

Process

Naturally occurring process:

Biological process:

Cellular process:

Cell signaling

Role

Industrial application:

Biological role:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	6.56	ALOGPS
logP	9.95	ChemAxon
logS	-7.4	ALOGPS
pKa (Strongest Acidic)	1.86	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	77.05 Å²	ChemAxon
Rotatable Bond Count	40	ChemAxon
Refractivity	237.18 m³·mol⁻¹	ChemAxon
Polarizability	93.83 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9120232300-19053aae13a84480bd5d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052k-9373274000-b09a290fa630b2076c0f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-007a-9062153000-c89ef35164d9ced46b1d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0060003900-e74a999b3e619fc0559c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-1090206100-4cc859ff8fe827154e72	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-016r-5191500000-e161eba351c917d962ed	Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Feces
Saliva
Urine

Tissue Locations

All Tissues

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	44.5 (37.6-53.3) uM	Newborn (0-30 days old)	Not Available	Normal	25754623	details
Blood	Detected and Quantified	267.03(66.1) uM	Adult (>18 years old)	Both	Normal	26010610	details
Blood	Detected and Quantified	212 (183-244) uM	Infant (0-1 year old)	Not Available	Normal	25754623	details
Blood	Detected and Quantified	250.7 +/- 47.2 uM	Adult (>18 years old)	Both	Normal	28278231	details
Feces	Detected and Quantified	0.84 +/- 2 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Feces	Detected and Quantified	1.46 +/- 2.13 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Saliva	Detected and Quantified	0.200 +/- 0.031 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Urine	Detected and Quantified	0.016 (0.0021-0.045) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	220.75(59.14) uM	Adult (>18 years old)	Both	Heart failure with preserved ejection fraction	26010610	details
Blood	Detected and Quantified	192.7 +/- 50.0 uM	Children (1-13 years old)	Both	Obesity	Metabolomics reve...	details
Blood	Detected and Quantified	233.6 +/- 68.4 uM	Children (1-13 years old)	Both	Obesity	Metabolomics reve...	details
Blood	Detected and Quantified	155.673 (140.706) uM	Adult (>18 years old)	Female	Pregnancy with fetus having congenital heart defect	24704061	details
Blood	Detected and Quantified	279.018 (74.520) uM	Adult (>18 years old)	Female	Pregnancy	24704061	details
Feces	Detected but not Quantified	Not Quantified	Newborn (0-30 days old)	Not Specified	Premature neonates	23210743	details
Feces	Detected but not Quantified	Not Quantified	Newborn (0-30 days old)	Not Specified	Premature neonates	23210743	details

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 +/- 0.000 uM	Adult (>18 years old)	Both	Normal (Most Probable)	Calculated using MetaboAnalyst
Blood	0.417 +/- 0.161 uM	Adult (>18 years old)	Both	Normal (Upper Limit)	Calculated using MetaboAnalyst

Associated Disorders and Diseases

Disease References

Pregnancy
Bahado-Singh RO, Ertl R, Mandal R, Bjorndahl TC, Syngelaki A, Han B, Dong E, Liu PB, Alpay-Savasan Z, Wishart DS, Nicolaides KH: Metabolomic prediction of fetal congenital heart defect in the first trimester. Am J Obstet Gynecol. 2014 Sep;211(3):240.e1-240.e14. doi: 10.1016/j.ajog.2014.03.056. Epub 2014 Apr 1. [PubMed:24704061 ]
Obesity
Simone Wahl, Christina Holzapfel, Zhonghao Yu, Michaela Breier, Ivan Kondofersky, Christiane Fuchs, Paula Singmann, Cornelia Prehn, Jerzy Adamski, Harald Grallert, Thomas Illig, Rui Wang-Sattler, Thomas Reinehr (2013). Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children. Metabolomics.

Associated OMIM IDs

601665 (Obesity)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131801673

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Only showing the first 10 proteins. There are 44 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Calcium-dependent phospholipase A2

General function:: Involved in phospholipase A2 activity
Specific function:: PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. This isozyme hydrolyzes more efficiently L-alpha-1-palmitoyl-2-oleoyl phosphatidylcholine than L-alpha-1-palmitoyl-2-arachidonyl phosphatidylcholine, L-alpha-1-palmitoyl-2-arachidonyl phosphatidylethanolamine, or L-alpha-1-stearoyl-2-arachidonyl phosphatidylinositol. May be involved in the production of lung surfactant, the remodeling or regulation of cardiac muscle.
Gene Name:: PLA2G5
Uniprot ID:: P39877
Molecular weight:: 15674.065

Enzyme Details

2. Group IIF secretory phospholipase A2

General function:: Involved in phospholipase A2 activity
Specific function:: PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Hydrolyzes phosphatidylglycerol versus phosphatidylcholine with a 15-fold preference.
Gene Name:: PLA2G2F
Uniprot ID:: Q9BZM2
Molecular weight:: 23256.29

Enzyme Details

3. Cytosolic phospholipase A2

General function:: Involved in metabolic process
Specific function:: Selectively hydrolyzes arachidonyl phospholipids in the sn-2 position releasing arachidonic acid. Together with its lysophospholipid activity, it is implicated in the initiation of the inflammatory response.
Gene Name:: PLA2G4A
Uniprot ID:: P47712
Molecular weight:: 85210.19

Enzyme Details

4. Phospholipase A2

General function:: Involved in phospholipase A2 activity
Specific function:: PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides.
Gene Name:: PLA2G1B
Uniprot ID:: P04054
Molecular weight:: 16359.535

Enzyme Details

5. Group 10 secretory phospholipase A2

General function:: Involved in phospholipase A2 activity
Specific function:: PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a powerful potency for releasing arachidonic acid from cell membrane phospholipids. Prefers phosphatidylethanolamine and phosphatidylcholine liposomes to those of phosphatidylserine.
Gene Name:: PLA2G10
Uniprot ID:: O15496
Molecular weight:: 18153.04

Enzyme Details

6. Group IIE secretory phospholipase A2

General function:: Involved in phospholipase A2 activity
Specific function:: PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a preference for arachidonic-containing phospholipids.
Gene Name:: PLA2G2E
Uniprot ID:: Q9NZK7
Molecular weight:: 15988.525

Enzyme Details

7. Group XIIA secretory phospholipase A2

General function:: Involved in phospholipase A2 activity
Specific function:: PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Does not exhibit detectable activity toward sn-2-arachidonoyl- or linoleoyl-phosphatidylcholine or -phosphatidylethanolamine.
Gene Name:: PLA2G12A
Uniprot ID:: Q9BZM1
Molecular weight:: 21066.99

Enzyme Details

8. Phosphatidylcholine-sterol acyltransferase

General function:: Involved in phosphatidylcholine-sterol O-acyltransferase activity
Specific function:: Central enzyme in the extracellular metabolism of plasma lipoproteins. Synthesized mainly in the liver and secreted into plasma where it converts cholesterol and phosphatidylcholines (lecithins) to cholesteryl esters and lysophosphatidylcholines on the surface of high and low density lipoproteins (HDLs and LDLs). The cholesterol ester is then transported back to the liver. Has a preference for plasma 16:0-18:2 or 18:O-18:2 phosphatidylcholines. Also produced in the brain by primary astrocytes, and esterifies free cholesterol on nascent APOE-containing lipoproteins secreted from glia and influences cerebral spinal fluid (CSF) APOE- and APOA1 levels. Together with APOE and the cholesterol transporter ABCA1, plays a key role in the maturation of glial-derived, nascent lipoproteins. Required for remodeling high-density lipoprotein particles into their spherical forms.
Gene Name:: LCAT
Uniprot ID:: P04180
Molecular weight:: 49577.545

Enzyme Details

9. Phospholipase A2, membrane associated

General function:: Involved in phospholipase A2 activity
Specific function:: Thought to participate in the regulation of the phospholipid metabolism in biomembranes including eicosanoid biosynthesis. Catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides.
Gene Name:: PLA2G2A
Uniprot ID:: P14555
Molecular weight:: 16082.525

Enzyme Details

10. Group IID secretory phospholipase A2

General function:: Involved in phospholipase A2 activity
Specific function:: PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. L-alpha-1-palmitoyl-2-linoleoyl phosphatidylethanolamine is more efficiently hydrolyzed than the other phospholipids examined.
Gene Name:: PLA2G2D
Uniprot ID:: Q9UNK4
Molecular weight:: 16546.1

Only showing the first 10 proteins. There are 44 proteins in total.

Show all enzymes and transporters

Showing metabocard for PC(P-18:1(11Z)/P-18:1(11Z)) (HMDB0011300)

Structure for HMDB0011300 (PC(P-18:1(11Z)/P-18:1(11Z)))

Enzymes